The no-holds-barred tale of a Chicago-based thirty-something living the so-called dream

Once again, I’ve been pretty much MIA. Go figure, right? It’s for good reason though because I was on vacation, and for the two weeks since I’ve been back I’ve been attempting to play catch-up at the office. You never realize just how many emails you get each day until you take six days plus a weekend off with no access to company email/voicemail. But yes, I know you find it hard to believe, but even I need a well-deserved break sometimes. So on that note, I’m going to also take a break from writing about things that annoy me and weave you the tale (or more appropriately a poncho) of my recent friendcation to Mexico. I’m sure those of you who know me in person are like “Oh god, we have to hear about Mexico AGAIN?! Can’t you just shut up and move there already?” but I don’t care. This isn’t about you. Deal with it.

So here we are last summer when a friend asked me what I was doing in February. Funny, right? Half the time I don’t even know what I’m doing for dinner. So naturally, the minute he said “We’re looking at getting a group of friends together and booking a house in Puerto Vallarta for a week, you in?” Of course I was all in. I mean, you’d have to be crazy to say no to a week away from the frigid tundra otherwise known as Chicago in the winter.

Fast forward six months and the daily photo countdown kicks off on Facebook.

28 days…

23 days…

12 days. ..

…and and all the way on down until one day left. I’m sure every single one of our friends (of all eight of us going) were sufficiently annoyed by this point and probably relieved that we’d be finally ending the daily countdown of photos showcasing the sand, palm trees, ocean, and all the other things that go along with a vacation on the beach that we’d be experiencing and they wouldn’t. Did we care though? Not in the least. So long, suckers. My passport was ready in a feisty yellow leather case (with orange leather lining). My rainbow Lacoste beach towel was packed inside my brand new (white) suitcase that was filled to the brim with tank tops, flip flops, shorts, and the obligatory blow dryer just in case there wasn’t one where we were staying. My weave was freshly cut, and my brows and back waxed (just to be proactive/paranoid). The day had come, and it was time for this homo to blow this popsicle stand and make a beeline to paradise for a week. Hasta la vista.

Now you’re probably thinking…oh boy…he’s screwed. He’ll never survive in Mexico on a booze-fueled vacation with seven other hot messes. He probably can’t even speak Spanish!

Ha! Fooled ya!

Having taken Spanish all four years in high school, I was ready to conquer this country like a modern-day Cortez. I mean, hey, if my three Hispanic coworkers could manage to get me brushed up on my key phrases in six months then it was game on. I knew all the basics:

So away I went. Taxi to bus to Blue Line to O’Hare…to Houston…to Puerto Vallarta.

But time out…what’s a vacation for me (or going anywhere in public in general) without some ridiculous occurrence with some whacko? Yes, I know I said I was taking a break from writing about things that annoy me, but this guy in line at security….oh girl….what a clown.

So here I am in line at security at 4:45am when Captain Douchebag in front of me starts complaining that the line is too long and how it’s ridiculous that there’s only one security checkpoint open. Across the way, you can see TSA milling around getting ready to open another checkpoint. At this point, he starts snapping his fingers (yes, really) and going “Hey, hey you!” to the uniformed dominatrix of a TSA agent to get her attention. What I would’ve paid right then to see her bust out the nightstick on him. He continues on to complain “I know that they’re getting ready to open over there. They always open the second checkpoint at 5am. Why can’t we just go over there?” to which she responds “Sir, when they open we’ll pull some of you over there, but unfortunately you’ll have to wait in line with everyone else unless you have Priority Boarding which you clearly don’t or else you wouldn’t be in this line.”

Well played, ma’am, well played.

You’d think that’d shut this idiot down and shut him up. Nope. Not at all. For the next 15 minutes, he continues to complain to anyone and everyone around him who cared (or didn’t care) about his dilemma of having to wait in line….when finally, at 5am, the other security checkpoint opens. Cue the snapping of the fingers.

As fate – or more likely karma – would have it, Nightstick Nancy came over just as she said she would and let about 30 people move over to the other line…about 29 of which were right in front of him….making him wait, huffing and puffing the whole time nonetheless, in line behind the stanchion. I couldn’t help but smile as she winked at me, both of us knowing fully well how annoyed he was that he was being made to wait even longer.

Finally, she let him (and me and a bunch of other people behind us) migrate over. You’d think he’d be happy to be moving, but instead he utters to no one in particular “This is ridiculous. I fly 2-3 round-trip flights a month out of here. They always open this checkpoint at 5am. I don’t understand why we have to wait in line.” And because I’m never one to keep my mouth shut, I respond:

“Well, sir, if you fly so often wouldn’t you typically catch onto the fact that they open at 5am and show up to the airport 15 minutes later so you don’t have to stand in line like a normal person?”

Oh whoops? Sorry not sorry. Jackass.

But wait, there’s more! As we get up to the security checkpoint and he puts his items on the belt…it all of a sudden comes to a halt. Yes, the belt broke and we had to move over to the next conveyor. I thought he was about to have a coronary. Needless to say, he finally got through security. Who knows where he was going, but at least he wasn’t on my flight.

So anyways. Puerto Vallarta.

After some hardcore people watching/drooling over some straight frat boys at the airport and on my flight – and texting about said individuals including creeptastic picture messages with one of the other guys going on the trip who ended up being only one gate and a ten-minute difference in flight times away – I made it to Houston. It’s never too early for cocktails on vacation, right? I mean, it’s like 8am. Surely he’ll want a cocktail while we wait for our next flight, right? Right, yes. Legal, no. I made the discovery that I was going on vacation with a 19-year old. Holy shit. It’s like I’m going on vacation with my little sister. Seriously. They are the same age!

Needless to say, we made it to Mexico and THANK GOD he’s bilingual because I wouldn’t have made it to the house we’d rented….about 5 miles south of town, not to mention the drive TO town from the airport, then up a hill with a cab driver who barely spoke English. Let’s just say it’s a good thing his parents were from Belize and Mexico or we would have been lost. Literally.

After we finally got to the house, we were met by our housekeeper who was in the middle of making us fresh guacamole and pico de gallo, guacamole that has officially ruined me by the way since I’ll never find guacamole as good as hers ever again. She showed us around our 6 bedroom, 5 bathroom palace of a house complete with a pool and volleyball court…and a poolside bar…all with a view of the ocean from all four levels of the house. Insane, right?

Since we were the first ones there and the other six wouldn’t be there for a few hours, we took the opportunity to house half of the guacamole, test out the pool, and call dibs on rooms that we’d eventually end up switching anyway. It was like we’d been picked to be on MTV’s The Real World: Puerto Vallarta. Eight strangers, picked to live in a house, blah blah blah. For real though, I only knew three of the guys going and had hung out with the one girl maybe once or twice. This was bound to be an adventure – especially with two couples, two single bottoms, and two straight girls with boyfriends back in the States. I mean, what could go wrong (or so right) with six gays and two girls?

The modern misadventures of a twentysomething transplant from Nebraska, trying to navigate Chicago. Many gays love meddling with my life, for better and for worse. Fortunately, I'm a less horse-faced version of Carrie Bradshaw, that, unfortunately, never gets any action.